ChemSpider 2D Image | Seliciclib | C19H26N6O

Seliciclib

  • Molecular FormulaC19H26N6O
  • Average mass354.449 Da
  • Monoisotopic mass354.216797 Da
  • ChemSpider ID140922
  • defined stereocentres - 1 of 1 defined stereocentres


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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(+)-Seliciclib
(2R)-2-{[6-(benzylamino)-9-(propan-2-yl)-9H-purin-2-yl]amino}butan-1-ol
(2R)-2-{[6-(Benzylamino)-9-isopropyl-9H-purin-2-yl]amino}-1-butanol [ACD/IUPAC Name]
(2R)-2-{[6-(Benzylamino)-9-isopropyl-9H-purin-2-yl]amino}-1-butanol [German] [ACD/IUPAC Name]
(2R)-2-{[6-(Benzylamino)-9-isopropyl-9H-purin-2-yl]amino}-1-butanol [French] [ACD/IUPAC Name]
(2R)-2-{[6-(Benzylamino)-9-isopropyl-9H-purin-2-yl]amino}butan-1-ol
(R)-Roscovitine
0ES1C2KQ94
186692-46-6 [RN]
1-Butanol, 2-[[9-(1-methylethyl)-6-[(phenylmethyl)amino]-9H-purin-2-yl]amino]-, (2R)- [ACD/Index Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

AIDS022527 [DBID]
AIDS-022527 [DBID]
Bio1_000302 [DBID]
Bio1_000791 [DBID]
Bio1_001280 [DBID]
Bio2_000379 [DBID]
Bio2_000859 [DBID]
CBiol_002016 [DBID]
CYC 202 [DBID]
CYC-202 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Target Organs:

      CDK inhibitor TargetMol T2095
    • Chemical Class:

      2,6-Diaminopurine carrying benzylamino, (2<stereo>R</stereo>)-1-hydroxybutan-2-yl and isopropyl substituents at C-6, C-2-N and N-9 respectively. It is an experimental drug candidate in the family of p harmacological cyclin-dependent kinase (CDK) inhibitors. ChEBI CHEBI:45307
    • Bio Activity:

      Cdc2/CDK2/CDK5 TargetMol T2095
      CDK MedChem Express HY-30237
      Cell Cycle/Checkpoint TargetMol T2095
      Cell Cycle/DNA Damage MedChem Express HY-30237
      Cell Cycle/DNA Damage; MedChem Express HY-30237
      Cyclin-dependent Kinase Tocris Bioscience 1332
      Enzymes Tocris Bioscience 1332
      Kinases Tocris Bioscience 1332
      Potent, selective cyclin-dependent kinase inhibitor Tocris Bioscience 1332
      Potent, selective inhibitor of cyclin-dependent kinases (cdk). Inhibits cdc2/cyclin B (IC50 = 650 nM), cdk2/cyclin A (IC50 = 700 nM), cdk2/cyclin E (IC50 = 700 nM), cdk5 / p35 (IC50 = 160 nM) and is selective over cdk4/cyclin D1 and cdk6/cyclin D3 (IC50 > 100 ?M). Also selective over a wide range of related kinases including ERK1 and ERK2. Arrests L1210 cells in G1 phase. Inhibits phosphorylation of vimentin in vivo. Antimitotic. Tocris Bioscience 1332
      Potent, selective inhibitor of cyclin-dependent kinases (cdk). Inhibits cdc2/cyclin B (IC50 = 650 nM), cdk2/cyclin A (IC50 = 700 nM), cdk2/cyclin E (IC50 = 700 nM), cdk5 / p35 (IC50 = 160 nM) and is selective over cdk4/cyclin D1 and cdk6/cyclin D3 (IC50 > 100 muM). Also selective over a wide range of related kinases including ERK1 and ERK2. Arrests L1210 cells in G1 phase. Inhibits phosphorylation of vimentin in vivo. Antimitotic. Tocris Bioscience 1332
      Roscovitine (Seliciclib, CYC202) is a potent and selective CDK inhibitor for Cdc2, CDK2 and CDK5 with IC50 of 0.65 ?M, 0.7 ?M and 0.16 ?M; shows little effect on CDK4/6.; IC50 Value: 0.65 ?M(Cdc2); 0.7 ?M(CDK2); 0.16 ?M(CDK5); Target: Cdc2/CDK2/CDK5; in vitro: Roscovitine displays high efficiency and high selectivity towards some cyclin-dependent kinases with IC50 of 0.65, 0.7, 0.7 and 0.16 ?M for cdc2/cyclin B, cdk2/cyclin A, cdk2/cyclin E and cdk5/p53, respectively. MedChem Express HY-30237

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.3±0.1 g/cm3
Boiling Point: 577.5±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.7 mmHg at 25°C
Enthalpy of Vaporization: 90.9±3.0 kJ/mol
Flash Point: 303.1±32.9 °C
Index of Refraction: 1.643
Molar Refractivity: 102.0±0.5 cm3
#H bond acceptors: 7
#H bond donors: 3
#Freely Rotating Bonds: 8
#Rule of 5 Violations: 0
ACD/LogP: 1.68
ACD/LogD (pH 5.5): 4.38
ACD/BCF (pH 5.5): 1213.21
ACD/KOC (pH 5.5): 5368.99
ACD/LogD (pH 7.4): 4.45
ACD/BCF (pH 7.4): 1414.27
ACD/KOC (pH 7.4): 6258.75
Polar Surface Area: 88 Å2
Polarizability: 40.4±0.5 10-24cm3
Surface Tension: 47.4±7.0 dyne/cm
Molar Volume: 281.9±7.0 cm3

Predicted data is generated using the US Environmental Protection Agency’s EPISuite™

                        
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  3.11

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  554.96  (Adapted Stein & Brown method)
    Melting Pt (deg C):  238.27  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.88E-014  (Modified Grain method)
    Subcooled liquid VP: 3.78E-012 mm Hg (25 deg C, Mod-Grain method)

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  12.93
       log Kow used: 3.11 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  504.46 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Imidazoles

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.10E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  6.781E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.11  (KowWin est)
  Log Kaw used:  -14.347  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  17.457
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.3981
   Biowin2 (Non-Linear Model)     :   0.0511
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3279  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.2539  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.5043
   Biowin6 (MITI Non-Linear Model):   0.0004
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.4670
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  5.04E-010 Pa (3.78E-012 mm Hg)
  Log Koa (Koawin est  ): 17.457
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  5.95E+003 
       Octanol/air (Koa) model:  7.03E+004 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 248.5785 E-12 cm3/molecule-sec
      Half-Life =     0.043 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.516 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 1 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  4313
      Log Koc:  3.635 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
    Rate constants can NOT be estimated for this structure!

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 1.042 (BCF = 11.03)
       log Kow used: 3.11 (estimated)

 Volatilization from Water:
    Henry LC:  1.1E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.002E+013  hours   (4.175E+011 days)
    Half-Life from Model Lake : 1.093E+014  hours   (4.555E+012 days)

 Removal In Wastewater Treatment:
    Total removal:               6.74  percent
    Total biodegradation:        0.13  percent
    Total sludge adsorption:     6.61  percent
    Total to Air:                0.00  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.000309        1.03         1000       
   Water     12.5            900          1000       
   Soil      87.1            1.8e+003     1000       
   Sediment  0.365           8.1e+003     0          
     Persistence Time: 1.79e+003 hr




                    

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